Aqua­(2,2′-bipyridine)bis­(4-hydroxy­benzoato)zinc(II)

Zhang, B.-Y.; Nie, J.-J.; Xu, D.-J.

doi:10.1107/S1600536809025525

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m880

doi:10.1107/S1600536809025525

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Aqua(2,2′-bipyridine)bis(4-hydroxybenzoato)zinc(II)

Bing-Yu Zhang,^a Jing-Jing Nie ^a and Duan-Jun Xu ^a ^*

^aDepartment of Chemistry, Zhejiang University, Hangzhou, 310027, People's Republic of China
^*Correspondence e-mail: xudj@mail.hz.zj.cn

(Received 27 June 2009; accepted 1 July 2009; online 8 July 2009)

In the title complex, [Zn(C₇H₅O₃)₂(C₁₀H₈N₂)(H₂O)], the Zn^II ion is coordinated by two 4-hydroxybenzoate anions, one 2,2′-bipyridine molecule and one water molecule and displays a distorted octahedral geometry. One Zn—O bond [2.5300 (15) Å] is much longer than the others in the molecule. In the crystal structure, the face-to-face separation of 3.547 (9) Å suggests no π–π stacking between parallel bipyridine ring systems, and an extensive O—H⋯O hydrogen-bonding network between the coordinated water molecule, the phenol group and carboxylate O atoms is present.

Related literature

For general background, see: Xu et al. (2007a ,b ); Li et al. (2005 ). For a related structure, see: Kong et al. (2008 ). For the smaller metal—O—C bond angle corresponding to the longer coordination bond, see: Li et al. (2005).

Experimental

Crystal data

[Zn(C₇H₅O₃)₂(C₁₀H₈N₂)(H₂O)]
M_r = 513.79
Monoclinic, P 2₁ /c
a = 10.3549 (12) Å
b = 19.524 (3) Å
c = 11.5544 (18) Å
β = 107.97 (2)°
V = 2221.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 294 K
0.40 × 0.32 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.659, T_max = 0.724
13723 measured reflections
5092 independent reflections
3794 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.084
S = 1.07
5092 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn—O1	2.5300 (15)
Zn—O2	2.0045 (14)
Zn—O4	2.0607 (14)
Zn—O7	2.1375 (15)
Zn—N1	2.0986 (18)
Zn—N2	2.1275 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.94	1.64	2.565 (2)	169
O6—H6A⋯O4ⁱⁱ	0.87	1.81	2.668 (2)	168
O7—H7A⋯O3ⁱⁱⁱ	0.90	1.93	2.813 (2)	168
O7—H7B⋯O5	0.95	1.73	2.636 (2)	158
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025525/hk2727sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025525/hk2727Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigation on the nature of π-π stacking (Xu et al., 2007a, 2007b; Li et al., 2005), the title complex was prepared in the laboratory and its crystal structure is reported herein.

The molecular structure of the title complex is shown in Fig. 1. The Zn^II cation is coordinated by two 4-hydroxybenzoate anions, one 2,2-bipyridine and one water molecules with a distorted octahedral geometry. The Zn—O1 [2.5300 (15) Å] bond is much longer than the other Zn—O bonds in the molecule (Table 1), but the smaller Zn–O2–C1 [103.38 (13)°] bond angle suggests the existence of a genuine bonding between O1 and Zn atoms (Li et al. 2005). This is similar to that in aqua-(4-hydroxybenzoato)(4-hydroxybenzoato) (1,10-phenanthroline)zinc monohydrate (Kong et al., 2008).

In the crystal structure, extensive O—H···O hydrogen bonding occurs (Table 2) and the longer face-to-face separation of 3.547 (9) Å between parallel bipyridine ligands, related by an inversion center, suggests no π-π stacking.

Related literature top

For general background, see: Xu et al. (2007a,b); Li et al. (2005). For a related structure, see: Kong et al. (2008). For the smaller metal–O–C bond angle, see: Li et al. (2005).

Experimental top

ZnCl₂ (0.136 g, 1 mmol), 4-hydroxybenzoic acid (0.14 g, 1 mmol), Na₂CO₃ (0.053 g, 0.5 mmol) and 2,2-bipyridine (0.156 g, 1 mmol) were dissolved in a water/ethanol solution (20 ml, 2:3). The mixture was refluxed for 4 h, and then cooled to room temperature and filtered. Colorless single crystals were obtained from the filtrate after 10 d.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title complex with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). The dashed line indicates the intramolecular hydrogen bonding.

Aqua(2,2'-bipyridine)bis(4-hydroxybenzoato)zinc(II) top

Crystal data top

[Zn(C₇H₅O₃)₂(C₁₀H₈N₂)(H₂O)]	F(000) = 1056
M_r = 513.79	D_x = 1.536 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8786 reflections
a = 10.3549 (12) Å	θ = 2.8–25.0°
b = 19.524 (3) Å	µ = 1.16 mm⁻¹
c = 11.5544 (18) Å	T = 294 K
β = 107.97 (2)°	Prism, colorless
V = 2221.9 (6) Å³	0.40 × 0.32 × 0.28 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5092 independent reflections
Radiation source: fine-focus sealed tube	3794 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
ω scans	h = −13→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −16→25
T_min = 0.659, T_max = 0.724	l = −15→14
13723 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0381P)² + 0.2291P] where P = (F_o² + 2F_c²)/3
5092 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Zn(C₇H₅O₃)₂(C₁₀H₈N₂)(H₂O)]	V = 2221.9 (6) Å³
M_r = 513.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3549 (12) Å	µ = 1.16 mm⁻¹
b = 19.524 (3) Å	T = 294 K
c = 11.5544 (18) Å	0.40 × 0.32 × 0.28 mm
β = 107.97 (2)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5092 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3794 reflections with I > 2σ(I)
T_min = 0.659, T_max = 0.724	R_int = 0.028
13723 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
5092 reflections	Δρ_min = −0.31 e Å⁻³
307 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn	0.72142 (2)	0.523813 (12)	0.76441 (2)	0.03203 (9)
N1	0.71413 (18)	0.55972 (9)	0.93348 (15)	0.0364 (4)
N2	0.50939 (18)	0.52685 (8)	0.74053 (16)	0.0326 (4)
O1	0.79866 (17)	0.40502 (8)	0.84339 (14)	0.0472 (4)
O2	0.72447 (15)	0.44341 (7)	0.65740 (13)	0.0390 (4)
O3	0.90448 (17)	0.14372 (8)	0.55801 (14)	0.0503 (4)
H3A	0.8612	0.1314	0.4770	0.075*
O4	0.69289 (14)	0.60029 (7)	0.63604 (13)	0.0349 (3)
O5	0.88734 (15)	0.59867 (8)	0.59074 (13)	0.0419 (4)
O6	0.53361 (16)	0.81021 (8)	0.20163 (14)	0.0473 (4)
H6A	0.5940	0.8348	0.1816	0.071*
O7	0.93531 (15)	0.53817 (7)	0.80380 (14)	0.0418 (4)
H7A	0.9755	0.5746	0.8475	0.063*
H7B	0.9281	0.5502	0.7227	0.063*
C1	0.7783 (2)	0.39661 (10)	0.73229 (19)	0.0329 (5)
C2	0.8162 (2)	0.33111 (10)	0.68419 (18)	0.0293 (4)
C3	0.8999 (2)	0.28391 (10)	0.76110 (18)	0.0329 (5)
H3	0.9367	0.2942	0.8434	0.039*
C4	0.9297 (2)	0.22205 (11)	0.71799 (18)	0.0359 (5)
H4	0.9871	0.1911	0.7706	0.043*
C5	0.8738 (2)	0.20608 (10)	0.59584 (19)	0.0342 (5)
C6	0.7894 (2)	0.25250 (11)	0.51718 (19)	0.0359 (5)
H6	0.7508	0.2417	0.4354	0.043*
C7	0.7633 (2)	0.31490 (10)	0.56143 (18)	0.0329 (5)
H7	0.7093	0.3467	0.5081	0.040*
C8	0.7700 (2)	0.61981 (10)	0.57269 (18)	0.0315 (5)
C9	0.7101 (2)	0.67051 (10)	0.47486 (18)	0.0323 (5)
C10	0.5709 (2)	0.67839 (12)	0.4277 (2)	0.0418 (5)
H10	0.5143	0.6516	0.4579	0.050*
C11	0.5143 (2)	0.72511 (12)	0.3370 (2)	0.0442 (6)
H11	0.4205	0.7292	0.3059	0.053*
C12	0.5968 (2)	0.76610 (11)	0.29181 (19)	0.0360 (5)
C13	0.7366 (2)	0.75963 (11)	0.3390 (2)	0.0402 (5)
H13	0.7928	0.7875	0.3103	0.048*
C14	0.7924 (2)	0.71194 (11)	0.42857 (19)	0.0386 (5)
H14	0.8863	0.7073	0.4585	0.046*
C15	0.8215 (3)	0.56939 (13)	1.0329 (2)	0.0484 (6)
H15	0.9075	0.5584	1.0290	0.058*
C16	0.8100 (3)	0.59469 (14)	1.1398 (2)	0.0607 (7)
H16	0.8866	0.6009	1.2069	0.073*
C17	0.6831 (3)	0.61079 (14)	1.1463 (2)	0.0614 (8)
H17	0.6727	0.6286	1.2176	0.074*
C18	0.5722 (3)	0.60022 (13)	1.0462 (2)	0.0532 (7)
H18	0.4855	0.6105	1.0492	0.064*
C19	0.5899 (2)	0.57419 (10)	0.9407 (2)	0.0367 (5)
C20	0.4749 (2)	0.55895 (11)	0.82961 (19)	0.0359 (5)
C21	0.3423 (3)	0.57615 (13)	0.8165 (2)	0.0528 (6)
H21	0.3199	0.5984	0.8788	0.063*
C22	0.2426 (3)	0.55975 (15)	0.7089 (3)	0.0590 (7)
H22	0.1526	0.5715	0.6981	0.071*
C23	0.2768 (3)	0.52628 (13)	0.6190 (2)	0.0512 (6)
H23	0.2111	0.5142	0.5468	0.061*
C24	0.4112 (2)	0.51086 (12)	0.6382 (2)	0.0424 (5)
H24	0.4351	0.4882	0.5770	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.03499 (15)	0.02836 (14)	0.03540 (15)	0.00098 (10)	0.01475 (11)	−0.00214 (10)
N1	0.0381 (11)	0.0359 (10)	0.0350 (10)	−0.0019 (8)	0.0111 (8)	−0.0014 (8)
N2	0.0357 (10)	0.0325 (10)	0.0333 (9)	−0.0021 (7)	0.0159 (8)	−0.0029 (8)
O1	0.0717 (12)	0.0333 (9)	0.0397 (9)	0.0048 (8)	0.0215 (8)	−0.0022 (7)
O2	0.0454 (9)	0.0282 (8)	0.0428 (9)	0.0082 (7)	0.0128 (7)	0.0003 (7)
O3	0.0730 (12)	0.0339 (9)	0.0415 (9)	0.0193 (8)	0.0141 (8)	−0.0036 (7)
O4	0.0375 (8)	0.0302 (8)	0.0424 (8)	0.0048 (6)	0.0204 (7)	0.0063 (6)
O5	0.0306 (9)	0.0527 (10)	0.0440 (9)	0.0025 (7)	0.0140 (7)	0.0054 (7)
O6	0.0439 (10)	0.0430 (9)	0.0572 (10)	−0.0002 (7)	0.0186 (8)	0.0184 (8)
O7	0.0359 (9)	0.0431 (9)	0.0450 (9)	−0.0054 (7)	0.0103 (7)	0.0000 (7)
C1	0.0329 (11)	0.0263 (11)	0.0414 (12)	−0.0033 (9)	0.0142 (10)	−0.0021 (9)
C2	0.0296 (11)	0.0252 (10)	0.0364 (11)	−0.0009 (8)	0.0149 (9)	0.0000 (8)
C3	0.0352 (12)	0.0324 (11)	0.0311 (11)	0.0012 (9)	0.0102 (9)	−0.0009 (9)
C4	0.0408 (13)	0.0321 (12)	0.0341 (11)	0.0101 (9)	0.0105 (9)	0.0062 (9)
C5	0.0407 (13)	0.0275 (11)	0.0387 (12)	0.0044 (9)	0.0187 (10)	−0.0004 (9)
C6	0.0410 (13)	0.0375 (12)	0.0293 (11)	0.0051 (9)	0.0109 (9)	−0.0023 (9)
C7	0.0339 (12)	0.0301 (11)	0.0357 (12)	0.0064 (9)	0.0121 (9)	0.0054 (9)
C8	0.0338 (12)	0.0277 (11)	0.0337 (11)	−0.0056 (9)	0.0115 (9)	−0.0065 (9)
C9	0.0339 (12)	0.0300 (11)	0.0345 (11)	−0.0029 (9)	0.0126 (9)	0.0000 (9)
C10	0.0355 (13)	0.0440 (13)	0.0496 (14)	−0.0061 (10)	0.0186 (11)	0.0098 (11)
C11	0.0295 (12)	0.0501 (14)	0.0534 (14)	−0.0022 (10)	0.0133 (10)	0.0146 (11)
C12	0.0407 (13)	0.0311 (11)	0.0381 (12)	−0.0024 (9)	0.0151 (10)	0.0023 (9)
C13	0.0374 (13)	0.0403 (13)	0.0460 (14)	−0.0113 (10)	0.0172 (10)	0.0052 (10)
C14	0.0305 (12)	0.0433 (13)	0.0426 (13)	−0.0080 (9)	0.0121 (10)	0.0016 (10)
C15	0.0475 (15)	0.0535 (16)	0.0415 (14)	−0.0066 (11)	0.0099 (11)	0.0007 (12)
C16	0.069 (2)	0.0658 (19)	0.0397 (15)	−0.0206 (15)	0.0060 (13)	−0.0063 (13)
C17	0.087 (2)	0.0605 (18)	0.0409 (15)	−0.0099 (15)	0.0252 (15)	−0.0159 (13)
C18	0.0646 (18)	0.0538 (16)	0.0480 (15)	0.0030 (13)	0.0274 (13)	−0.0110 (12)
C19	0.0453 (13)	0.0275 (11)	0.0409 (12)	0.0003 (9)	0.0186 (10)	−0.0009 (9)
C20	0.0392 (13)	0.0331 (12)	0.0399 (12)	0.0009 (9)	0.0187 (10)	0.0001 (10)
C21	0.0457 (15)	0.0651 (17)	0.0541 (16)	0.0074 (12)	0.0249 (13)	−0.0058 (13)
C22	0.0365 (14)	0.075 (2)	0.0681 (19)	0.0054 (13)	0.0194 (13)	0.0037 (15)
C23	0.0399 (14)	0.0640 (18)	0.0464 (14)	−0.0067 (12)	0.0082 (11)	0.0046 (13)
C24	0.0448 (14)	0.0463 (14)	0.0377 (12)	−0.0075 (11)	0.0151 (11)	−0.0042 (10)

Geometric parameters (Å, º) top

Zn—O1	2.5300 (15)	C7—H7	0.9300
Zn—O2	2.0045 (14)	C8—C9	1.486 (3)
Zn—O4	2.0607 (14)	C9—C10	1.383 (3)
Zn—O7	2.1375 (15)	C9—C14	1.396 (3)
Zn—N1	2.0986 (18)	C10—C11	1.377 (3)
Zn—N2	2.1275 (17)	C10—H10	0.9300
N1—C15	1.343 (3)	C11—C12	1.384 (3)
N1—C19	1.344 (3)	C11—H11	0.9300
N2—C24	1.337 (3)	C12—C13	1.386 (3)
N2—C20	1.344 (3)	C13—C14	1.379 (3)
O1—C1	1.246 (2)	C13—H13	0.9300
O2—C1	1.264 (2)	C14—H14	0.9300
O3—C5	1.364 (2)	C15—C16	1.369 (3)
O3—H3A	0.9362	C15—H15	0.9300
O4—C8	1.295 (2)	C16—C17	1.375 (4)
O5—C8	1.239 (2)	C16—H16	0.9300
O6—C12	1.355 (2)	C17—C18	1.371 (4)
O6—H6A	0.8744	C17—H17	0.9300
O7—H7A	0.8971	C18—C19	1.384 (3)
O7—H7B	0.9465	C18—H18	0.9300
C1—C2	1.494 (3)	C19—C20	1.487 (3)
C2—C3	1.384 (3)	C20—C21	1.376 (3)
C2—C7	1.390 (3)	C21—C22	1.386 (4)
C3—C4	1.377 (3)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.364 (4)
C4—C5	1.386 (3)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.373 (3)
C5—C6	1.386 (3)	C23—H23	0.9300
C6—C7	1.380 (3)	C24—H24	0.9300
C6—H6	0.9300

O1—Zn—O2	56.03 (5)	O5—C8—C9	120.47 (18)
O1—Zn—O4	152.01 (5)	O4—C8—C9	116.13 (18)
O1—Zn—O7	81.49 (6)	C10—C9—C14	118.02 (19)
O1—Zn—N1	93.94 (6)	C10—C9—C8	120.87 (18)
O1—Zn—N2	105.73 (6)	C14—C9—C8	121.11 (19)
O2—Zn—O4	98.60 (6)	C11—C10—C9	121.4 (2)
O2—Zn—O7	91.23 (6)	C11—C10—H10	119.3
O2—Zn—N1	147.97 (7)	C9—C10—H10	119.3
O2—Zn—N2	98.85 (6)	C10—C11—C12	120.2 (2)
O4—Zn—O7	88.12 (6)	C10—C11—H11	119.9
O4—Zn—N1	112.93 (6)	C12—C11—H11	119.9
O4—Zn—N2	88.48 (6)	O6—C12—C11	116.7 (2)
N1—Zn—O7	95.19 (7)	O6—C12—C13	123.98 (19)
N1—Zn—N2	77.25 (7)	C11—C12—C13	119.3 (2)
N2—Zn—O7	169.74 (6)	C14—C13—C12	120.1 (2)
Zn—O1—C1	79.34 (12)	C14—C13—H13	119.9
Zn—O2—C1	103.38 (13)	C12—C13—H13	119.9
Zn—O4—C8	130.04 (13)	C13—C14—C9	121.0 (2)
C15—N1—C19	118.2 (2)	C13—C14—H14	119.5
C15—N1—Zn	125.83 (16)	C9—C14—H14	119.5
C19—N1—Zn	115.97 (14)	N1—C15—C16	122.9 (2)
C24—N2—C20	118.50 (19)	N1—C15—H15	118.6
C24—N2—Zn	125.52 (15)	C16—C15—H15	118.6
C20—N2—Zn	114.88 (14)	C15—C16—C17	118.8 (2)
C5—O3—H3A	117.6	C15—C16—H16	120.6
C12—O6—H6A	109.7	C17—C16—H16	120.6
Zn—O7—H7A	119.6	C18—C17—C16	119.0 (2)
Zn—O7—H7B	93.5	C18—C17—H17	120.5
H7A—O7—H7B	104.0	C16—C17—H17	120.5
O1—C1—O2	120.60 (19)	C17—C18—C19	119.6 (2)
O1—C1—C2	121.04 (19)	C17—C18—H18	120.2
O2—C1—C2	118.36 (18)	C19—C18—H18	120.2
C3—C2—C7	118.38 (18)	N1—C19—C18	121.4 (2)
C3—C2—C1	121.02 (18)	N1—C19—C20	115.53 (19)
C7—C2—C1	120.54 (18)	C18—C19—C20	123.0 (2)
C4—C3—C2	121.16 (19)	N2—C20—C21	121.4 (2)
C4—C3—H3	119.4	N2—C20—C19	115.06 (19)
C2—C3—H3	119.4	C21—C20—C19	123.5 (2)
C3—C4—C5	119.73 (19)	C20—C21—C22	119.0 (2)
C3—C4—H4	120.1	C20—C21—H21	120.5
C5—C4—H4	120.1	C22—C21—H21	120.5
O3—C5—C4	117.50 (18)	C23—C22—C21	119.8 (2)
O3—C5—C6	122.40 (19)	C23—C22—H22	120.1
C4—C5—C6	120.10 (19)	C21—C22—H22	120.1
C7—C6—C5	119.36 (19)	C22—C23—C24	118.1 (2)
C7—C6—H6	120.3	C22—C23—H23	120.9
C5—C6—H6	120.3	C24—C23—H23	120.9
C6—C7—C2	121.23 (19)	N2—C24—C23	123.2 (2)
C6—C7—H7	119.4	N2—C24—H24	118.4
C2—C7—H7	119.4	C23—C24—H24	118.4
O5—C8—O4	123.39 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.94	1.64	2.565 (2)	169
O6—H6A···O4ⁱⁱ	0.87	1.81	2.668 (2)	168
O7—H7A···O3ⁱⁱⁱ	0.90	1.93	2.813 (2)	168
O7—H7B···O5	0.95	1.73	2.636 (2)	158

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₅O₃)₂(C₁₀H₈N₂)(H₂O)]
M_r	513.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	10.3549 (12), 19.524 (3), 11.5544 (18)
β (°)	107.97 (2)
V (Å³)	2221.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.40 × 0.32 × 0.28

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.659, 0.724
No. of measured, independent and observed [I > 2σ(I)] reflections	13723, 5092, 3794
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.07
No. of reflections	5092
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.31

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Zn—O1	2.5300 (15)	Zn—O7	2.1375 (15)
Zn—O2	2.0045 (14)	Zn—N1	2.0986 (18)
Zn—O4	2.0607 (14)	Zn—N2	2.1275 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.94	1.64	2.565 (2)	169
O6—H6A···O4ⁱⁱ	0.87	1.81	2.668 (2)	168
O7—H7A···O3ⁱⁱⁱ	0.90	1.93	2.813 (2)	168
O7—H7B···O5	0.95	1.73	2.636 (2)	158

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+2, y+1/2, −z+3/2.

Acknowledgements

The project was supported by the ZIJIN project of Zhejiang University, China.

References

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